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PubMed2002

The regulation of COQ5 gene expression by energy source.

The degree of severity of cardiomyopathy is inversely correlated with tissue levels of coenzyme Q (Q), suggesting that Q synthesis may impact the progression of the disease. It has been suggested that Q functions as an endogenously synthesized anti-oxidant, in addition to regenerating the potent anti-oxidants, vitamins E and C. However, very little is known about the mechanisms that regulate Q synthesis. Using the simple eukaryote Saccharomyces cerevisiae as a model, experiments have been designed to investigate the regulation of Q synthesis at the genetic level. To investigate the regulation of COQ5 gene expression by energy source, mRNA content was evaluated in yeast cells treated with dextrose, glycerol or oleic acid. After 1.5 h, more COQ5 mRNA is produced by oleic acid treated cells than by glycerol treated. Experiments performed using COQ5 promoter deletion/reporter constructs demonstrate a specific response to oleic acid. Additional promoter deletion analysis demonstrates that a non-fermentable carbon source element is also present, responding to both glycerol and oleic acid. The specific oleic acid response appears to be regulated by the Rtg family of transcription factors. This family of proteins is required for oleic acid-induced expression of genes of beta-oxidation and peroxisomal proliferation, and plays an important role in co-ordinating mitochondrial/peroxisomal/nuclear communication in response to oleic acid, as well as defects in cellular respiration.

Basic Helix-Loop-Helix Leucine Zipper Transcriptio↗
PubMed1976

Incorporation of fatty acids containing photosensitive groups into phospholipids of Escherichia coli.

A series of new fatty acids containing photosensitive groups at different positions on the paraffin chains supported the growth of an auxotroph of E. coli requiring unsaturated fatty acids. The derivatives were 6-, 9-, 11-, and 12-azidostearic acids, 12-azido-oleic acid, 16-azidopalmitelaidic acid, and 12-(4-azido-2-nitrophenoxy)-stearic and -oleic acids. Analyses of the phospholipids from cultures grown in the presence of the first six compounds showed that these derivatives accounted for 16-43% of the total fatty acids. Further analysis of phospholipids from cultures grown with 12-azido-oleic acid, 11-azidostearic acid, or 16-azidopalmitelaidic acid indicated that the azido fatty acids were at the 2-position of the glycerol moieties. The incorporation of these fatty acid derivatives offers a new approach to the study of membrane structure and, in particular, phospholipid-protein interactions by photolysis-induced crosslinking of the fatty acids to the structures in their immediate vicinity.

Azides↗
PubMed1978

Protein binding of tolmetin.

The protein binding of the new nonsteroidal anti-inflammatory agent tolmetin to human serum albumin (HSA) and to the plasma of 8 healthy subjects was studied by equilibrium dialysis at 37 degrees and pH 7.4 with 14C-tolmetin. Over the total concentration (Ct) range 3.0 to 28.7 microgram/ml (therapeutic range), the fraction of tolmetin unbound to 4% HSA was largely invariant at 0.3%. At 100 microgram/ml the unbound fraction rose to 0.8 and at 434 microgram/ml to 3.6%. Within the therapeutic concentration range, tolmetin binding to 0.4% HSA was reduced in accordance with the law of mass action and at Ct = 26.2 microgram/ml, 10.5% was free. Analysis of the 0.4% HSA data showed tolmetin had 3 classes of binding sites (n1 = 1, K1 = 8.3 X 10(5) M-1; n2 = 4, K2 = 2.4 X 10(4) M-1; n3 = 44, K1 = 7.9 X 10(1) M-1). By studying the binding to 0.4% HSA at 23 degrees, it was established that the free energy change in binding for the first two classes of sites was entirely entropic in nature. Albumin accounted for almost all the binding of tolmetin in human plasma. The effect of other drugs, the tolmetin metabolite McN 2987 (5-p-carboxybenzoyl-1-methylpyrrole-2-acetic acid), tryptophan, and oleic acid on tolmetin binding to 4% HSA was studied using ultrafiltration and 14C-tolmetin. Aspirin and salicyclic acid decreased tolmetin binding and a combination of aspirin and salicyclic acid exerted a synergistic displacing effect. Indomethacin and ibuprofen had no effect while phenylhbutazone and acetaminophen increased tolmetin binding slightly. Tolmetin binding was decreased slightly by McN 2987 and tryptophan and markedly increased by oleic acid. McN 2987 was not bound as extensively as tolmetin. Binding of 14C-tolmetin to the plasma of 4 arthritic patients was studied by ultrafiltration and found to be less than to normal plasma and 4% HSA. Distribution of tolmetin in the whole blood of 8 healthy subjects using a centrifugation technique showed that the drug was not taken up by red blood cells at therapeutic concentrations.

Adult↗
PubMed2000

Feeding oleamide to lactating Jersey cows. 2. Effects on nutrient digestibility, plasma fatty acids, and hormones.

Six lactating Jersey cows were used in a 6 x 6 Latin square with 14-d periods to evaluate different ratios of canola oil and oleamide on nutrient digestibility, plasma fatty acids, and plasma hormones. The control diet contained no added fat. All other diets contained 3.5% added fat consisting of 0, 25, 50, 75, and 100% as oleamide and the remainder as canola oil. Data were collected during the final 4 d of each period. Dry matter intake was reduced by the addition of canola oil to the diet, and further reduced by replacing canola oil with oleamide. Milk yield was not affected by diet but increasing oleamide proportion in the fat supplement caused linear increases in cis-C18:1 and linear decreases in C4 to C16 fatty acids in milk. Adding canola oil reduced total tract digestibilities of fiber and fatty acids, but had no effect on the digestibilities of dry matter or protein. Replacing canola oil with oleamide increased protein digestibility linearly, and increased digestibility of fiber (quartic relationship) and fatty acids (quadratic relationship). Oleic acid concentration in plasma increased by adding canola oil to the diet, and was further increased by replacing canola oil with oleamide. Diet had no effect on plasma concentrations of insulin or IGF-I. Oleamide fed to Jersey cows in this study was highly digestible and had no deleterious effects on total tract digestility of fiber or protein. Increasing oleic acid concentration in plasma lipids while maintaining a constant level of added fat in the ration had no effect on circulating concentrations of insulin or IGF-I in Jerseys.

Animals↗
PubMed1983

Qualitative and quantitative changes in milk fat during lactation in the tammar wallaby (Macropus eugenii).

There are major quantitative and qualitative changes in the milk lipids during lactation in the tammar wallaby, Macropus eugenii. The crude lipid content of the milk is relatively low during the first 10 weeks of lactation; between 10 and 26 weeks post partum the lipid content increases gradually but after that it increases rapidly. The triglyceride fraction of the lipid at early stages of lactation contains a large amount of palmitic acid and relatively little oleic acid whereas mature milk exhibits little palmitic and much oleic acid. In the early stages of lactation fat represents 15% of the total solids and carbohydrate 55%; around 26-30 weeks post partum the carbohydrate moiety falls sharply to a level less than 2% of the solids while lipids increase to c. 60% of the solids. These changes coincide with increases in milk solids, emergence of the young from the pouch, ingestion of herbage, and fermentation of cellulose in the stomach.

Animals↗
PubMed1993

[Protective effect of endothelin-antiserum on oleic acid-induced respiratory distress syndrome (RDS)].

On the rat RDS model produced by intravenous injection of oleic acid, , it was for the first time found that endothelin (ET) level in bronchoalveolar lavage fluid was elevated by 3-fold: and that preadministration of ET-antiserum to rat with RDS significantly improved its hypoxemia, pulmonary edema and histologic injury; inhibit the leakage of protein and intracellular enzymes from alveoli. The results suggest that ET might play an important role in the pathogenesis of RDS, and that treatment against ET would be a new approach for RDS.

Animals↗
PubMed1998

Single step thin-layer chromatographic method for quantitation of enzymatic formation of fatty acid anilides.

The activity of the enzyme involved in catalyzing the formation of fatty acid anilides can be measured by quantitating the fatty acid anilides formed. We have shown earlier that oleic acid is the most preferred substrate among other fatty acids studied for the conjugation with aniline. The reaction product (oleyl anilide) could be separated by thin-layer chromatography (TLC) and then quantified by reversed-phase high-performance liquid chromatography (HPLC). Using [1-(14)C]oleic acid as substrate, the fatty acid anilide forming activity can be determined in a single step by TLC analysis. The conventional TLC methods used for the separation of the fatty acid esters, however, could not resolve oleyl anilide from the residual [1-(14)C]oleic acid. Therefore, a simple and reliable TLC method was developed for the separation of oleyl anilide from oleic acid using a freshly prepared solvent consisting of petroleum ether-ethyl acetate-ammonium hydroxide (80:20:1, v/v). Using this solvent system the relative flow (Rf) values were found to be 0.54 for oleyl anilide and 0.34 for aniline, whereas oleic acid remained at the origin. The TLC procedure developed in the present study could be used to determine the fatty acid anilide forming activity using [1-(14)C]oleic or other fatty acids as substrate and was also found suitable for the analysis of fatty acid anilides from the biological samples.

Acyltransferases↗
PubMed2001

Eicosanoid production, thrombogenic ratio, and serum and LDL peroxides in normo- and hypercholesterolaemic post-menopausal women consuming two oleic acid-rich diets with different content of minor components.

The present paper compares the effects of two monounsaturated oils, extra virgin olive oil (EVOO) and high-oleic acid sunflower oil (HOSO), on serum and LDL peroxides, eicosanoid production and the thrombogenic ratio (thromboxane (TX) B2:6-keto-prostaglandin F1alpha) in fourteen non-obese post-menopausal women. The subjects, mean age 63 (SD 11) years, were assigned to two consecutive oleic acid-rich 28 d dietary periods. EVOO and HOSO represented 62 % of the total lipid intake and were used as the only culinary fat during the first and second dietary periods respectively. Serum peroxides, plasma alpha-tocopherol and TXB2 levels in stimulated platelet-rich plasma (PRP-TXB2) were significantly higher (P < 0.01, P < 0.001, and P < 0.05, respectively) after the HOSO diet than after the EVOO diet. The relationship between the serum cholesterol level (< 6.21 mmol/l or > or = 6.21 mmol/l) and the type of dietary oil on eicosanoids, peroxides and alpha-tocopherol were evaluated by two-way ANOVA. Dietary oil significantly affected (P < 0.05) the PRP-TXB2 level, whereas serum and LDL peroxides were significantly affected (P < 0.001 and P < 0.01, respectively) by the serum cholesterol level. The plasma alpha-tocopherol level was significantly affected by the serum cholesterol level and the type of dietary oil (both P < 0.001). No significant relationships were found between serum cholesterol levels, serum peroxide or LDL peroxide levels, plasma alpha-tocopherol concentrations or alpha-tocopherol intakes with eicosanoid production or the thrombogenic ratio due to dietary changes. However, in spite of their higher alpha-tocopherol levels, hypercholesterolaemic subjects showed increased peroxidation in serum and LDL in comparison with normocholesterolaemic subjects on the HOSO diet in comparison with the EVOO diet. These findings suggest that differences in the type of minor compounds, as well as in the concentration of linoleic acid, in both these monounsaturated oils may play an important role in modulating eicosanoid production and lipoprotein peroxidation when they constitute a large proportion of the diet of post-menopausal women.

Aged↗
PubMed1975

Oxidative desaturation of alpha-linoleic, linoleic, and stearic acids by human liver microsomes.

The desaturation of stearic, linoleic, and alpha-linolenic acids by human liver microsomes were studied. The microsomes were isolated from liver biopsies obtained during operation. It was shown that human liver microsomes are able to desaturate 1-14-C-alpha-linoleic acid to octadeca-6,9,12,15,-telraenoic acid: 1-15-C-linoleic acid to gammalinolenic acid; and 1-14-C-stearic acid to oleic acid in the same system described in the rat. However, the desaturation activity obtained was low compared to other mammals. This effect was attributed to fasting, pre-medication, or the anaesthesia.

Adult↗
PubMed1979

Esterification of exogenous and endogenous fatty acids by rat adipocytes in vitro.

Rat adipocytes were used in vivo to compare the esterification of exogenous fatty acids and fatty acids formed de novo from glucose or acetate. Pure single fatty acids added to the medium were esterified at comparable rates but marked differences were observed when the same acids were supplied as components of a fatty acid mixture of a composition similar to that in the tissue. Fatty acids synthesised de novo from acetate by adipocytes in a medium containing high concentrations of acetate were located predominantly in diacylglycerols. The effect was most marked with adipocytes from older rats and was enhanced by the presence of exogenous long-chain fatty acids. Exogenous oleic acid was esterified predominantly into triacylglycerols at all concentrations of acetate. No such accumulation of endogenously-synthesised fatty acids in diacylglycerols occurred when glucose was the precursor for fatty acid synthesis. The diacylglycerols formed were almost entirely of the sn-1,2-configuration.

Acetates↗
PubMed2003

Determination of fatty acid levels in erythrocyte membranes of patients with chronic fatigue syndrome.

Chronic fatigue syndrome (CFS) is an illness characterized by persistent and relapsing fatigue, often accompanied by numerous symptoms involving various systems of whole body. The etiology of CFS remains unclear. Literature reported whether the concentrations of the essential fatty acids in red cell membranes of CFS patients were decreased is controversial. In our study, Forty-two patients who fulfilled the diagnostic criteria defined by Centers for Disease Control and Prevention (CDC). Thirty-seven age- and sex-matched controls were selected from healthy medical staffs and volunteers. After lipid analysis, we found that the levels of the arachidonic acid (ARA) and docosahexanoic acid (DHA) were decreased in patients suffered from CFS. However, the levels of the palmitic acid and oleic acid were increased. We speculated that there are two possible mechanisms--one of which is that oxidative stress has led to an excessive oxidation and resulting in the above fatty acids. Alternatively, insufficiency of ingestion of fatty acids might not be the major cause.

Adult↗
PubMed2000

Effects of growth hormone treatment on red cell plasma membrane fatty acid constituents in hypopituitary adults.

The effects of replacement with recombinant human GH (hGH) on red cell plasma membrane fatty acid and cholesterol constituents were assessed in nine adult patients with growth hormone deficiency. They were treated with hGH in a dose of 0.125 U.kg-1.wk-1 for four weeks and at 0.25 U.kg-1.wk-1 thereafter for an overall mean duration 13.5 +/- 3.9 months (mean +/- SD). The relative proportions of the various phospholipid fatty acid constituents and the proportion of cholesterol in the phospholipid bilayer were assayed every six months. At the end of the study, the percentage of arachadonic acid (20:4) in membrane phospholipid was found to rise by an average of 3.7% (P < 0.05) and there appeared to be a nonsignificant trend showing an increase in highly unsaturated fatty acids, namely linoleate (18:2) and gamma linolenic acid (18:3) and a corresponding decrease in unsaturated fatty acids, namely palmitate (16:0) and stearate (18:0) and monounsaturated fatty acids such as palmitoleic acid (16:1), oleic acid (18:1) and oleic acid isomer (18:1 iso). In addition, the proportion of cholesterol in the plasma membrane i.e. the cholesterol/phospholipid ratio was found to decrease by 0.84% (P < 0.05). There was a significant increase in HbAlc from 4.85 +/- 0.51 to 4.94 +/- 0.45% (P < 0.01) by the end of the study.

Adult↗
PubMed1977

Effects of ascorbic acid and vitamin E on serum lipids of cockerels fed Wesson oil-cholesterol diets.

The major lipid changes caused by adding 5% Wesson Oil and 1% cholesterol to cockerel diets were large increases in serum cholesterol, cholesteryl esters, and triglycerides. Lecithin and cephalin were not affected. Ascorbic acid significantly increased serum triglycerides; vitamin E significantly lowered serum cholesterol. Percentages of the saturated acids (palmitic, stearic, and arachidonic) of cockerels on the Wesson Oil-cholesterol diet decreased significantly; unsaturated linolenic and linolenic acids increased, and oleic acid remained the same. Dietary ascorbic acid seemed not to affect fatty acid distribution significantly, but when vitamin E was added to the diet, the stearic acid percentage rose and oleic acid percentage was lower. Acrylamide-gel electrophoresis showed that changes the vitamin E caused in the lipid and protein constituents of cockerel serum differed from changes the Wesson Oil-cholesterol diet caused.

Animals↗
PubMed2006

Antihypertensive action of 2-hydroxyoleic acid in SHRs via modulation of the protein kinase A pathway and Rho kinase.

Olive oil consumption leads to high monounsaturated fatty acid intake, especially oleic acid, and has been associated with a reduced risk of hypertension. However, the molecular mechanisms and contribution of its different components to lower blood pressure (BP) require further evaluation. Here, we examined whether a synthetic, non-beta-oxidation-metabolizable derivative of oleic acid, 2-hydroxyoleic acid (2-OHOA), can normalize BP in adult spontaneously hypertensive rats (SHRs) and whether its antihypertensive action involves cAMP-dependent protein kinase A (PKA) and Rho kinase, two major regulators of vascular smooth muscle contraction. Oral administration of 2-OHOA to SHRs induced sustained systolic BP decreases in a time-dependent (1-7 days) and dose-dependent (100-900 mg/kg every 12 h) manner. After 7 days of treatment with 2-OHOA (600 mg/kg), the systolic BP of SHRs was similar to that of normotensive Wistar Kyoto rats, returning to its initial hypertensive level after withdrawal of 2-OHOA. This treatment strongly increased the protein expression of the catalytic and regulatory RIalpha and RIIalpha PKA subunits as well as PKA activity in aortas from SHRs. Consistently, administration of the PKA inhibitor 8-bromo adenosine-3',5'-cyclic monophosphorothioate, Rp isomer, to 2-OHOA-treated SHRs induced a pronounced reversal (up to 59%) of the antihypertensive effect of 2-OHOA. Additionally, 2-OHOA completely reversed the pathological overexpression of aortic Rho kinase found in SHRs, suppressing the vasoconstrictory Rho kinase pathway.

Adenylyl Cyclases↗
PubMed1984

Effect of free fatty acid on pulmonary transvascular fluid and protein exchange.

We demonstrated the effect of infusion of oleic acid, a common free fatty acid, on pulmonary vascular permeability in anesthetized dogs prepared with a lung lymph fistula. Infusion of oleic acid caused significant increases in lung lymph flow with no change in L/P protein ratio, resulting in significant increases in transvascular protein clearance. Pulmonary arterial and pulmonary arterial wedge pressures increased significantly from baseline but their elevation was slight. Cardiac output decreased significantly after oleic acid infusion. In contrast to the effects of oleic acid, left arterial hypertension caused increases in lung lymph flow that were associated with decreases in the L/P protein ratio. Lung water content was increased after oleic acid infusion, despite little effect on pulmonary vascular pressures. These findings indicate that oleic acid produced endothelial lung injury and increased pulmonary vascular permeability.

Animals↗
PubMed1985

The acute effects of intralipid on lung function.

To determine whether the oleic acid contained in intralipid injures the lung, we measured fractional lobar perfusion, lobar shunt, and edema (wet to dry weight ratios, W/D) in 20 open-chested mechanically ventilated dogs. Five dogs received oleic acid 0.03 g/kg injected into a lower lobe pulmonary artery. Ten received 0.5 cc/kg of 20% intralipid which contains the equivalent amount of oleic acid, five of these animals being heparinized. The same dose of oleic acid was also suspended in intralipid and administered to five heparinized dogs. Shunt and edema were measured in another five heparinized closed-chested dogs receiving 2 g/kg of intralipid IV over 1 hr. Half hour after intralipid or oleic acid, shunts did not change. At 2 1/2 hr, oleic acid alone increased lobar shunt from 4.6 +/- 1.4 to 40.8 +/- 24.9% while intralipid shunt remained unchanged with and without heparin. Lobar perfusion fell significantly with oleic acid from 29.3 +/- 2.3 to 17.8 +/- 5.6% while showing no change in the lobes not receiving oleic acid. When oleic acid was suspended in intralipid, shunt and perfusion changed less than with oleic acid alone. Mean W/D of the oleic acid lower lobe exceeded (P less than 0.05) W/D of the other lobes, including the lobe receiving oleic acid suspended in intralipid which had a W/D greater than the lobes receiving intralipid only. We conclude that intralipid has no acute deleterious effects on pulmonary gas exchange, blood flow distribution, or edema. Our data suggest that intralipid may protect the lung from the deleterious effects of fatty acids.

Animals↗
PubMed1987

Tubular complexes in cerulein- and oleic acid-induced pancreatitis in rats: glycoconjugate pattern, immunocytochemical, and ultrastructural findings.

Ductlike tubular complexes in cerulein-induced pancreatitis and oleic acid-induced pancreatic insufficiency were studied to analyze further their origin and development. Immunocytochemistry for pancreatic enzymes, lectin-binding studies, and ultrastructural investigations were combined with autoradiographic quantitation of labeling indices of ductlike cells in tubular complexes. In one group of rats, pancreatitis was induced by infusion of cerulein (10 micrograms kg-1 h-1). In a second group, pancreatic insufficiency was induced by intraductal injection of oleic acid (50 microliters). The investigations were carried out at distinct intervals following induction of pancreatic injury. In both groups of animals, after 3 days, a significant widening of acinar lumina was paralleled by a decreasing height of acinar cells, which showed pronounced retrogressive changes. At this time, acinar cells bound all of the lectins used and retained their immunoreactivity for amylase, trypsinogen, chymotrypsinogen, and lipase. At further intervals, acinar structures formed typical ductlike complexes, with a progressive loss of immunoreactivity for pancreatic enzymes and a reduced lectin-binding for L-fucose and N-acetylgalactosamine. Autoradiographic quantitation demonstrated no significant labeling of acinar cells undergoing tubular dedifferentiation. In both models, tubular complexes were removed by macrophages. It is concluded that lining cells in tubular complexes represent degenerating acinar cells that have no regenerative potency and have lost their secretory and membrane characteristics.

Animals↗
PubMed1982

Experimental diffuse alveolar damage in baboons.

Lung repair after diffuse alveolar damage (DAD) may be modified by supportive therapy or the occurrence of complications. To provide a clinically relevant model of DAD, we studied the feasibility of long-term respiratory support of 5 normal baboons and 20 baboons with oleic-acid-induced lung injury. Oleic acid caused DAD, which evolved through exudative and reparative phases similar to those seen in human disease. Fibrotic residuals were present at 1 month but resolved by 6 months. Pulmonary function abnormalities, including reduction in total lung capacity and diffusing capacity, and hypoxemia occurred with DAD but resolved within 1 month. Bronchopulmonary infection with gram-negative bacilli was a common and frequently fatal complication. Revisions in management of the upper airway and the use of topical polymyxin B prevented this complication. Other complications included hemorrhagic gastritis, postextubation, upper airway obstruction, and pulmonary embolism. This model simulates many features of DAD in humans and should provide a valuable resource for future study.

Acute Disease↗